diff --git a/.gitignore b/.gitignore
index 374deb4b..73aa79d1 100644
--- a/.gitignore
+++ b/.gitignore
@@ -61,3 +61,6 @@ coverage.xml
 .coverage
 .vscode/tasks.json
 todo.txt
+
+tags
+.vimrc
\ No newline at end of file
diff --git a/features/format.feature b/features/format.feature
index 77d36d71..20a4adc5 100644
--- a/features/format.feature
+++ b/features/format.feature
@@ -302,9 +302,9 @@ Feature: Custom formats
     Scenario Outline: Export fancy with small linewrap
         Given we use the config "<config>.yaml"
         And we use the password "test" if prompted
-        When we run "jrnl --config-override linewrap 12 --format fancy -3"
+        When we run "jrnl --config-override linewrap 35 --format fancy -3"
         Then we should get no error
-        And the output should be "12" columns wide
+        And the output should be 35 columns wide
         
         Examples: configs
         | config          |
diff --git a/features/steps/export_steps.py b/features/steps/export_steps.py
index f885591c..6ffd89af 100644
--- a/features/steps/export_steps.py
+++ b/features/steps/export_steps.py
@@ -12,6 +12,14 @@ from behave import given
 from behave import then
 
 
+@then("the output should be {width:d} columns wide")
+def check_output_width(context, width):
+    out = context.stdout_capture.getvalue()
+    out_lines = out.splitlines()
+    for line in out_lines:
+        assert len(line) <= width
+
+
 @then("the output should be parsable as json")
 def check_output_json(context):
     out = context.stdout_capture.getvalue()
diff --git a/jrnl/exception.py b/jrnl/exception.py
index 82a562a0..9c161992 100644
--- a/jrnl/exception.py
+++ b/jrnl/exception.py
@@ -30,7 +30,21 @@ class JrnlError(Exception):
 
                 Removing this file will allow jrnl to save its configuration.
             """
-            )
+            ),
+            "LineWrapTooSmallForDateFormat": textwrap.dedent(
+                """
+                The provided linewrap value of {config_linewrap} is too small
+                to display the timestamps in the configured time format.
+                """
+            ),
+            "LineWrapTooSmallForFancy": textwrap.dedent(
+                """
+                The provided linewrap value of {config_linewrap} is too small 
+                to properly format journal contents in fancy/boxed format. 
+                Either provide a larger value for the linewrap or display the
+                journal in another format.
+                """
+            ),
         }
 
         return error_messages[self.error_type].format(**kwargs)
diff --git a/jrnl/plugins/fancy_exporter.py b/jrnl/plugins/fancy_exporter.py
index 74cc6958..af6c19da 100644
--- a/jrnl/plugins/fancy_exporter.py
+++ b/jrnl/plugins/fancy_exporter.py
@@ -3,6 +3,7 @@
 # Copyright (C) 2012-2021 jrnl contributors
 # License: https://www.gnu.org/licenses/gpl-3.0.html
 
+from jrnl.exception import JrnlError
 from textwrap import TextWrapper
 
 from .text_exporter import TextExporter
@@ -14,12 +15,14 @@ class FancyExporter(TextExporter):
     names = ["fancy", "boxed"]
     extension = "txt"
 
+    # Top border of the card
     border_a = "┎"
     border_b = "─"
     border_c = "╮"
     border_d = "╘"
     border_e = "═"
     border_f = "╕"
+
     border_g = "┃"
     border_h = "│"
     border_i = "┠"
@@ -33,16 +36,18 @@ class FancyExporter(TextExporter):
         """Returns a fancy unicode representation of a single entry."""
         date_str = entry.date.strftime(entry.journal.config["timeformat"])
         linewrap = entry.journal.config["linewrap"] or 78
-        initial_linewrap = linewrap - len(date_str) - 2
+        initial_linewrap = max((1, linewrap - len(date_str) - 2))
         body_linewrap = linewrap - 2
         card = [
             cls.border_a + cls.border_b * (initial_linewrap) + cls.border_c + date_str
         ]
+        cls.check_linewrap(linewrap, card)
         w = TextWrapper(
             width=initial_linewrap,
             initial_indent=cls.border_g + " ",
             subsequent_indent=cls.border_g + " ",
         )
+
         title_lines = w.wrap(entry.title)
         card.append(
             title_lines[0].ljust(initial_linewrap + 1)
@@ -70,6 +75,13 @@ class FancyExporter(TextExporter):
         card.append(cls.border_l + cls.border_b * body_linewrap + cls.border_m)
         return "\n".join(card)
 
+    @classmethod
+    def check_linewrap(cls, linewrap, card):
+        if len(card[0]) > linewrap:
+            raise JrnlError("LineWrapTooSmallForDateFormat", config_linewrap=linewrap)
+        else:
+            pass
+
     @classmethod
     def export_journal(cls, journal):
         """Returns a unicode representation of an entire journal."""
diff --git a/tests/test_export.py b/tests/test_export.py
new file mode 100644
index 00000000..6419acb8
--- /dev/null
+++ b/tests/test_export.py
@@ -0,0 +1,39 @@
+from jrnl.exception import JrnlError
+from jrnl.plugins.fancy_exporter import FancyExporter
+
+
+import pytest
+
+
+@pytest.fixture()
+def datestr():
+
+    yield "2020-10-20 16:59"
+
+
+from textwrap import TextWrapper
+
+
+def provide_date_wrapper(initial_linewrap):
+    wrapper = TextWrapper(
+        width=initial_linewrap, initial_indent=" ", subsequent_indent=" "
+    )
+    return wrapper
+
+
+def build_card_header(datestr):
+    top_left_corner = "┎─╮"
+    content = top_left_corner + datestr
+    return content
+
+
+class TestFancy:
+    def test_too_small_linewrap(self, datestr):
+
+        content = build_card_header(datestr)
+
+        total_linewrap = 12
+
+        with pytest.raises(JrnlError) as e:
+            FancyExporter.check_linewrap(total_linewrap, [content])
+        assert e.value.error_type == "LineWrapTooSmallForDateFormat"